NP-MRD: Showing NP-Card for 4-(1-hydroxy-5-methylnaphthalen-2-yl)-2-methyl-4-oxobutyl acetate (NP0294428)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-10 02:57:44 UTC

Updated at

2022-09-10 02:57:44 UTC

NP-MRD ID

NP0294428

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-(1-hydroxy-5-methylnaphthalen-2-yl)-2-methyl-4-oxobutyl acetate

Description

4-(1-Hydroxy-5-methylnaphthalen-2-yl)-2-methyl-4-oxobutyl acetate belongs to the class of organic compounds known as naphthols and derivatives. These are naphthalene derivatives carrying one or more hydroxyl (-OH) groups at any ring position. 4-(1-hydroxy-5-methylnaphthalen-2-yl)-2-methyl-4-oxobutyl acetate is found in Salvia miltiorrhiza. 4-(1-Hydroxy-5-methylnaphthalen-2-yl)-2-methyl-4-oxobutyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 43  0  0  0  0  0  0  0  0999 V2000
   -7.0772    0.6081   -1.0719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6055    0.7122   -1.1673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0272    1.1537   -2.2073 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8229    0.3199   -0.0976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3939    0.4337   -0.2220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8086   -0.0546    1.0657 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1347   -1.4728    1.4104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3254    0.2487    1.0765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5494   -0.5590    0.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1919   -1.4141   -0.5587 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8815   -0.4655   -0.0547 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5186   -1.2720   -0.9684 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8773   -1.1987   -1.1717 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6321   -0.2951   -0.4451 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0023   -0.2297   -0.6585 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6443   -1.1175   -1.6523 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7145    0.6832    0.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1101    1.5053    1.0082 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7356    1.4220    1.2051 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9770    0.5227    0.4833 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6160    0.4648    0.7022 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9462    1.2579    1.6099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5020    1.2985   -1.8238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3987    0.7962   -0.0458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4415   -0.4073   -1.3462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2190    1.5329   -0.3231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0332   -0.1312   -1.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2218    0.6147    1.8893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3771   -2.0195    0.4891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2479   -1.9322    1.9140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9843   -1.4940    2.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9810    0.0421    2.1211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2562    1.3404    0.8932 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9696   -2.0024   -1.5681 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4110   -1.8208   -1.8850 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6963   -0.8032   -1.8002 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6967   -2.1816   -1.2772 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1589   -1.0901   -2.6445 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7838    0.7615   -0.0541 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6327    2.2271    1.6049 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2509    2.0710    1.9346 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3437    1.9451    2.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 11  1  0
 20 14  1  0
  7 29  1  0
  7 30  1  0
  7 31  1  0
  6 28  1  1
  5 26  1  0
  5 27  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  8 32  1  0
  8 33  1  0
 12 34  1  0
 13 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 22 42  1  0
M  END


  Mrv1533004191513252D          

 22 23  0  0  0  0            999 V2000
    7.1447   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  2  0  0  0  0
 11 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0294428

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(COC(C)=O)CC(=O)C1=CC=C2C(C)=CC=CC2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C18H20O4/c1-11(10-22-13(3)19)9-17(20)16-8-7-14-12(2)5-4-6-15(14)18(16)21/h4-8,11,21H,9-10H2,1-3H3

> <INCHI_KEY>
IEAVPUOPDGFUOO-UHFFFAOYSA-N

> <FORMULA>
C18H20O4

> <MOLECULAR_WEIGHT>
300.354

> <EXACT_MASS>
300.136159124

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
33.04454274616171

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(1-hydroxy-5-methylnaphthalen-2-yl)-2-methyl-4-oxobutyl acetate

> <ALOGPS_LOGP>
3.45

> <JCHEM_LOGP>
3.8947502910000007

> <ALOGPS_LOGS>
-4.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.326354257492383

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.74829372720155

> <JCHEM_PKA_STRONGEST_BASIC>
-5.315806725142221

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
84.71280000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.71e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(1-hydroxy-5-methylnaphthalen-2-yl)-2-methyl-4-oxobutyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0      13.337  -1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.003  -3.850   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       9.336  -3.850   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.670  -3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.004  -3.080   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      16.004  -1.540   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      17.338  -3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      18.672  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      20.005  -3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      20.005  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.339  -6.160   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      22.673  -5.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      21.339  -7.700   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      20.005  -8.470   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      18.672  -7.700   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      18.672  -6.160   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      17.338  -5.390   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      16.004  -6.160   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    2    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   21                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   20                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   14   21                                                  
CONECT   21   20   11   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Value	Source
4-(1-Hydroxy-5-methylnaphthalen-2-yl)-2-methyl-4-oxobutyl acetic acid	Generator

Chemical Formula

C₁₈H₂₀O₄

Average Mass

300.3540 Da

Monoisotopic Mass

300.13616 Da

IUPAC Name

4-(1-hydroxy-5-methylnaphthalen-2-yl)-2-methyl-4-oxobutyl acetate

Traditional Name

4-(1-hydroxy-5-methylnaphthalen-2-yl)-2-methyl-4-oxobutyl acetate

CAS Registry Number

Not Available

SMILES

CC(COC(C)=O)CC(=O)C1=CC=C2C(C)=CC=CC2=C1O

InChI Identifier

InChI=1S/C18H20O4/c1-11(10-22-13(3)19)9-17(20)16-8-7-14-12(2)5-4-6-15(14)18(16)21/h4-8,11,21H,9-10H2,1-3H3

InChI Key

IEAVPUOPDGFUOO-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Salvia miltiorrhiza	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthols and derivatives. These are naphthalene derivatives carrying one or more hydroxyl (-OH) groups at any ring position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Naphthols and derivatives

Direct Parent

Naphthols and derivatives

Alternative Parents

Substituents

Butyrophenone
1-naphthol
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
Vinylogous acid
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.45	ALOGPS
logP	3.89	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	8.75	ChemAxon
pKa (Strongest Basic)	-5.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	84.71 m³·mol⁻¹	ChemAxon
Polarizability	33.04 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11558483

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-(1-hydroxy-5-methylnaphthalen-2-yl)-2-methyl-4-oxobutyl acetate (NP0294428)

MOL for NP0294428 (4-(1-hydroxy-5-methylnaphthalen-2-yl)-2-methyl-4-oxobutyl acetate)

3D MOL for NP0294428 (4-(1-hydroxy-5-methylnaphthalen-2-yl)-2-methyl-4-oxobutyl acetate)

3D SDF for NP0294428 (4-(1-hydroxy-5-methylnaphthalen-2-yl)-2-methyl-4-oxobutyl acetate)

3D-SDF for NP0294428 (4-(1-hydroxy-5-methylnaphthalen-2-yl)-2-methyl-4-oxobutyl acetate)

PDB for NP0294428 (4-(1-hydroxy-5-methylnaphthalen-2-yl)-2-methyl-4-oxobutyl acetate)

3D PDB for NP0294428 (4-(1-hydroxy-5-methylnaphthalen-2-yl)-2-methyl-4-oxobutyl acetate)

SMILES for NP0294428 (4-(1-hydroxy-5-methylnaphthalen-2-yl)-2-methyl-4-oxobutyl acetate)

INCHI for NP0294428 (4-(1-hydroxy-5-methylnaphthalen-2-yl)-2-methyl-4-oxobutyl acetate)

Structure for NP0294428 (4-(1-hydroxy-5-methylnaphthalen-2-yl)-2-methyl-4-oxobutyl acetate)

3D Structure for NP0294428 (4-(1-hydroxy-5-methylnaphthalen-2-yl)-2-methyl-4-oxobutyl acetate)